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Vacation rental beach houses in Anna Maria

Vacation rental beach houses in Anna Maria

Book beachfront vacation rental houses, cottages, and more on Airbnb

Top-rated houses in Anna Maria

Guests agree: these stays are highly rated for location, cleanliness, and more.

Anna Maria Island Duplex w/ private pool (side B)
SUPERHOST
Entire house · 10 guests · 6 beds · 2 baths

Anna Maria Island Duplex w/ private pool (side B)Anna Maria Island duplex located in the Holmes Beach area. The side being rented sleeps 10, has its own private pool, is 3 blocks from beach access, 1 block from the free trolley stop & 1 block to Holmes Beach town center's restaurants, shopping & bars.

2-6 Day Available in Oct, Nov, Dec & Jan. 5-Stars!
SUPERHOST
Entire house · 8 guests · 5 beds · 2 baths

2-6 Day Available in Oct, Nov, Dec & Jan. 5-Stars!* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. * There's no better way to unwind and forget all your troubles, than staying at Sunshine Cottage, located in the City of Anna Maria!

Luxury 3BR/3BA, Private Heated Pool, Beach
SUPERHOST
Entire house · 6 guests · 5 beds · 3 baths

Luxury 3BR/3BA, Private Heated Pool, BeachRenovated and professionally decorated single family home that sleeps 8. 3 bedrooms and 3 full bathrooms. Living room with pullout couch as well as games, books and movie library. Luxurious heated pool with waterfall and Tiki table in private tropical backyard. Large covered lanai with TV, mini-fridge, granite counter for food preparation and gas BBQ. Large size Washer/Dryer. 4 minute easy stroll to beach. Attached garage. Low traffic street. Tons of toys as well as pool and beach supplies.

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Cottages
  • Apartments

Popular house amenities in Anna Maria

  • Pool
  • Pets allowed
  • Air conditioning
  • Kitchen
  • Wifi

Cottages in Anna Maria

Turtle Cottage - Anna Maria Island
SUPERHOSTEntire cottage
Turtle Cottage - Anna Maria Island
Price:R 3,118 ZAR / night
Adorable Pine Ave Cottage ❤️Walk to Beach and Bay!
SUPERHOSTEntire cottage
Adorable Pine Ave Cottage ❤️Walk to Beach and Bay!
Price:R 2,601 ZAR / night
'Elegance' 100 Steps from the Beach
Entire cottage
'Elegance' 100 Steps from the Beach
Price:R 5,197 ZAR / night
Harrington Bungalow 5 in the Heart of Anna Maria Island
Entire cottage
Harrington Bungalow 5 in the Heart of Anna Maria Island
Price:R 2,392 ZAR / night
Becker's Beach Bungalow
SUPERHOSTEntire cottage
Becker's Beach Bungalow
Price:R 2,380 ZAR / night
Palm Cottage in North Longboat Key
Entire cottage
Palm Cottage in North Longboat Key
Price:R 1,402 ZAR / night
Rest & Relax — Just One House Off The Beach
SUPERHOSTEntire cottage
Rest & Relax — Just One House Off The Beach
Price:R 2,557 ZAR / night
50 Steps to Beach🏖.  Hot Tub! 1bd modern cottage🏝
SUPERHOSTEntire cottage
50 Steps to Beach🏖. Hot Tub! 1bd modern cottage🏝
Price:R 3,712 ZAR / night
Bay Breeze Cottages #2
SUPERHOSTEntire cottage
Bay Breeze Cottages #2
Price:R 4,226 ZAR / night
Beach Cottage with private garden
SUPERHOSTEntire cottage
Beach Cottage with private garden
Price:R 2,062 ZAR / night
MorSea Cottage: A Beachside Oasis
Entire cottage
MorSea Cottage: A Beachside Oasis
Price:R 4,018 ZAR / night
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK!
Entire cottage
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK!
Price:R 3,811 ZAR / night
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Pet-friendly houses

Twin Palms: Big house steps to beach, private pool
SUPERHOSTEntire house
Twin Palms: Big house steps to beach, private pool
Price:R 4,283 ZAR / night
Beachfront Private Beach, Dogs ok, Backyard beach
Entire house
Beachfront Private Beach, Dogs ok, Backyard beach
Price:R 4,537 ZAR / night
Dog-friendly home with private pool, great location near beach, shopping, dining
Entire house
Dog-friendly home with private pool, great location near beach, shopping, dining
Price:R 3,712 ZAR / night
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
SUPERHOSTEntire house
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
Price:R 5,597 ZAR / night
AMI Boathouse
SUPERHOSTEntire house
AMI Boathouse
Price:R 6,111 ZAR / night
Island in the Sun
SUPERHOSTEntire house
Island in the Sun
Price:R 4,999 ZAR / night
⭐️ Seaside Sanctuary ⭐️ fischervacationrentals
SUPERHOSTEntire house
⭐️ Seaside Sanctuary ⭐️ fischervacationrentals
Price:R 3,283 ZAR / night
⭐️Escape to Anna Maria ⭐️ fischervacationrentals
SUPERHOSTEntire house
⭐️Escape to Anna Maria ⭐️ fischervacationrentals
Price:R 3,283 ZAR / night
Dog friendly oasis with private pool and very close to the beach
Entire house
Dog friendly oasis with private pool and very close to the beach
Price:R 4,306 ZAR / night
The Anna Maria Beach Cottage - East
SUPERHOSTEntire house
The Anna Maria Beach Cottage - East
Price:R 1,895 ZAR / night
Salty Dogs Beach House-SPECIAL Rate Oct 24- Nov 4
SUPERHOSTEntire house
Salty Dogs Beach House-SPECIAL Rate Oct 24- Nov 4
Price:R 5,333 ZAR / night
Top-rated Anna Maria, Florida Vacation Rental
SUPERHOSTEntire house
Top-rated Anna Maria, Florida Vacation Rental
Price:R 4,124 ZAR / night
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Houses with pools

Family Fun Close to Beach, Pool Slide Spa & Elevator
Entire house
Family Fun Close to Beach, Pool Slide Spa & Elevator
Price:R 6,823 ZAR / night
Golf cart +4bd/2b w large outdoor pool/shower/deck
SUPERHOSTEntire house
Golf cart +4bd/2b w large outdoor pool/shower/deck
Price:R 5,067 ZAR / night
Spectacular home 700 feet from the beach!
SUPERHOSTEntire house
Spectacular home 700 feet from the beach!
Price:R 2,364 ZAR / night
Walk 2 Beach + PRIVATE Pool + Golf Cart + Boating
SUPERHOSTEntire house
Walk 2 Beach + PRIVATE Pool + Golf Cart + Boating
Price:R 4,725 ZAR / night
Anna Cabana B
SUPERHOSTEntire house
Anna Cabana B
Price:R 2,970 ZAR / night
The Sandbox
Entire house
The Sandbox
Price:R 4,128 ZAR / night
Incredible, spacious home with a private heated pool - close to the beach!
Entire house
Incredible, spacious home with a private heated pool - close to the beach!
Price:R 4,091 ZAR / night
Beachfront Oasis - Elegant beach front home! Views for days, private pool, beach access!
Entire house
Beachfront Oasis - Elegant beach front home! Views for days, private pool, beach access!
Price:R 8,117 ZAR / night
Large AMI Beach Home (Heated Pool)
Entire house
Large AMI Beach Home (Heated Pool)
Price:R 4,702 ZAR / night
BEACH NEST *Pool*Hot Tub*Dock*Steps to Gulf Beach!
SUPERHOSTEntire house
BEACH NEST *Pool*Hot Tub*Dock*Steps to Gulf Beach!
Price:R 7,047 ZAR / night
AMI Retreat
SUPERHOSTEntire house
AMI Retreat
Price:R 4,461 ZAR / night
New Prof Decor-Pool/Spa 5 Mn walk 2 ocean Discount
SUPERHOSTEntire house
New Prof Decor-Pool/Spa 5 Mn walk 2 ocean Discount
Price:R 4,956 ZAR / night
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Nearby destinations